Industrial Product Service Systems (IPS²) are an innovative business model for engineering enterprises; integrating products and services. A substantial portion of later operating costs is determined by decisions in the design phase. This leads to a hierarchical problem structure: On the strategic planning level; configuration of IPS² is accomplished regarding customers’ requirements and uncertainties. Revenues and (adaptation) costs during the subsequent delivery phase have to be anticipated. The operative planning level is concerned with the use of a given IPS². Later changes of business models are only possible within the scope of the strategic plan. The more uncertainties strategic planning faces; the more flexibility has to be provided in order to assure a successful coordination of both levels.